Methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate → Methyl 1-(2-amino-4-formylphenyl)piperidine-4-carboxylate

HRID 1801586

反応式

HRID 1801586 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]2)=[C:5]([N+:19]([O-])=O)[CH:4]=1)=[O:2].[H][H]>[Pd].CCOC(C)=O>[NH2:19][C:5]1[CH:4]=[C:3]([CH:1]=[O:2])[CH:8]=[CH:7][C:6]=1[N:9]1[CH2:10][CH2:11][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:14]1

参加物

5

反応物 2

HCID 9111291Methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 59803213Methyl 1-(2-amino-4-formylphenyl)piperidine-4-carboxylate収率 15.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 10% palladium on carbon (1.67 g, 1.57 mmol) and methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate 58 (3.435 g, 11.8 mmol) was added EtOAc (100 mL). The nitrogen atmosphere was replaced by hydrogen from a double balloon and the reaction mixture was stirred at room temperature for 4 h, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 20% to 60% EtOAc in hexanes) gave methyl 1-(2-amino-4-formylphenyl)piperidine-4-carboxylate 59 (0.488 g, 15.8% yield) as a yellow solid. Mass spectrum: calculated for C14H18N2O3 262.1. found 263.2 (M++1).

後処理

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customPurification by flash column chromatography on silica gel (eluted with 20% to 60% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-70c987bf522a4faa96f8f03cc2e62987
出典データセット
uspto-grants-2013_01
特許番号
US08349831B2

関連ノート

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